Emulsifiable concentrate for a low dosage fluorinated agricultural chemical

ABSTRACT

An effective emulsifiable concentrate for a low dosage fluorinated agricultural chemical, e.g. diflufenican, a herbicide, in optional admixture with a diluent active agricultural chemical, e.g. bromoxynil octanoate or isooctylmetachlorophenyl acetate herbicides is described herein.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to liquid delivery systems for activeagricultural chemicals, and, more particularly, to an emulsifiableconcentrate for delivering an admixture of a low dosage fluorinatedagricultural chemical and a diluent active agricultural chemical to aplant site.

2. Description of the Prior Art

Emulsion concentrates are favored liquid delivery systems for activeagricultural chemicals. See Narayanan U.S. Pat. Nos. 5,231,070;5,298,529; 5,317,042; and 5,389,297.

An emulsifiable concentrate (EC) is a solution of the agchemical,solvents and surfactants that when diluted with water forms an emulsionwhich can be sprayed onto crops. An EC is needed for most agchemicalsbecause they are usually water insoluble. Such concentrates are easy tostore and transport, and various adjuvants may be added to increase theefficacy of the formulation. A good EC, however, requires that a stableemulsion be formed upon dilution with water, which emulsion does notseparate upon standing. Furthermore, there should not be anycrystallization of the active from the EC after water dilution. Inaddition, the EC itself must be stable with little degradation of theactive over a long shelf life, and over a range of storage temperatures.

A poor EC is generally recognized by poor emulsion stability wherein themicelles of the emulsion are observed to coalesce upon water dilution,and by rapid crystal formation therein. For such ECs, it is necessary toadd a crystal inhibitor, or, more likely, to reformulate the EC. Asuitably reformulated EC thus must solubilize the active in a suitablesolvent system which must also be sufficiently hydrophobic so that theactive remains in the micelle and does not migrate into the water phaseof the emulsion.

Accordingly, it is an object of this invention to provide an effectiveEC for an admixture of a low dosage, water-insoluble fluorinated activeagricultural chemical and a diluent agricultural chemical.

These and other objects and features of the invention will be madeapparent from the following more particular description of theinvention.

SUMMARY OF THE INVENTION

What is provided herein is an EC for an admixture of a low dosage,water-insoluble fluorinated active agricultural chemical, such asdiflufenican herbicide, and, optionally, a diluent active agriculturalchemical such as bromoxynil octanoate or isooctyl-metachlorophenylacetate herbicides which includes by weight, (a) about 20-60% of such anadmixture of low dosage active and diluent active; (b) about 2-15% of ananionic surfactant, such as an ethoxylated nonyl phenol phosphate ester;optionally including 0-10% of a non-ionic surfactant, such asethoxylated castor oil; and (c) about 15-30% of a C₆ -C₁₈ alkylpyrrolidone; optionally including 0-10% of a C₁ -C₄ alkyl pyrrolidone orgamma-butyrolactone, and 0-30% of a C₆ -C₈ alkyl acetate.

DETAILED DESCRIPTION OF THE INVENTION

In accordance with the invention, the primary active agriculturalchemical which has been formulated into a useful EC, is an admixture ofa low dosage, water-insoluble fluorinated agricultural chemical, such asdiflufenican, and, optionally, a diluent active agricultural chemical,such as bromoxynil octanoate. A typical admixture in the EC formulationincludes about 2.6% diflufenican and about 37.1% bromoxynil octanoate.Other active agricultural chemicals as secondary diluents also may beincluded within this mixture if desired.

The EC composition thus includes (a) about 20-60% of the admixture ofactive agricultural chemicals; (b) about 2-15% of an anionic surfactant,suitably an ethoxylated nonyl phenol phosphate ester; optionally with upto about 10% of a non-ionic surfactant, suitably an ethoxylated castoroil; (c) about 15-30% of a C₆ -C₁₈ alkyl pyrrolidone, most suitablyN-octyl pyrrolidone, N-isooctyl pyrrolidone or N-dodecyl pyrrolidone, ormixtures thereof, N-octyl pyrrolidone being preferred, optionallyincluding up to 10% of a C₁ -C₄ alkyl pyrrolidone orgamma-butyrolactone, and optionally up to 30% of a C₆ -C₈ alkyl acetate.

EXAMPLES OF FLUORINATED ACTIVE INGREDIENTS AND DILUENTS

(A) Fluorinated active ingredients

Fluorinated Herbicides/Insecticides

Herbicides

FLURTAMONE (Chevron)

FLUMETSULAM (Dow Elanco)

CLODINAFOP-PROPARGYL (Ciba Geigy)

THIAZOPYR (Monsanto/Rhom AND Haas)

FLURPRIMIDOL (Dow Elanco)

ETHOXYFEN-ETHYL (Budapest Chemical)

FLUTHIACET-METHYL (Kumiai Chemical/Ihara Chemical)

SULFENTRAZONE (FMC)

FLUPOXAM (Kureha Chemical/Monsanto)

FLUMIOXAZIN (Sumitomo)

ISOXAFLUTOLE (FMC)

CARFENTRAZONE-ETHYL (FMC)

Herbicides (Diluents):

METOLACHLOR (Ciba Geigy)

TRIFLURALIN (Dow Elanco)

CHLOPYRALID (Dow Elanco)

2,4, D (Several Companies)

CLODINAFOP-PROPARGYL (Ciba Geigy)

ISOPROTURON (Rhone Poulenc)

DIURON (Rhone Poulenc)

DSMA (Disodium Methane Arsonate), and MSMA (Monosodium Methane Arsonate)

Insecticides

FIPRONIL (Rhone Poulenc)

FLUFENOXURON (Ciba Geigy)

FLUVALINATE (Sandoz)

FLUCYTHRINATE (Du Pont)

CYFLUTRRIN (Bayer)

TEFLUTHRIN (ICI)

BIFENTHRIN (FMC)

DIFLUBENZURON (Duphar, Netharlands)

TRIFLUMURON (Bayer)

CHLORFLURAZUM (Ciba Geigy/Ishihara)

Insecticides (Diluents)

CARBARYL (Rhone Poulenc)

PERMETHRIN (Several)

PIPERONYL BUTOXIDE (Several)

HYDRAMETHYLNON (Am. Cy)

DIAZINON (Ciba Geigy)

ALDECARB (Union Carbide)

Fungicides

FLUOROMIDE (Mitsubhishi)

FLUTRIAFOL (ICI)

FLUTOLANIL (Nihaku Nohyaku, Japan)

FLUSILAZOL (Du Pont)

TRIFLUMIZOLE (Nippon Soda Co)

Fungicide (Diluents)

PROPICONAZOLE (Ciba Geigy)

PENCONAZOLE (Ciba Geigy)

TRIFORINE (CelamercK, Germany)

THIABENDAZOLE (Merck)

DACONIL (ISK Biotech)

MANCOZEB (Rhom and Haas)

Plant Growth Regulators/Repellents/Rodenticides

FLUMETRALIN (Ciba Geigy)

FLURPRIMIDOL (Dow Elanco)

EFLUIDIDE (3M)

FLURAZOLE (Monsanto)

BROMETHALIN (Eli Lilly)

Plant Growth Regulators/Repellents/Rodenticides--Diluents

THIRAM (TETRAMETHYL THIURAM DISULFIDE)--(Du Pont)

ETHEPHON (Rhone Poulenc)

The EC compositions thus-prepared are shown in Table 1 below. The degreeof stability of such EC compositions upon dilution with water (1:50) isgiven in Table 2 below.

                  TABLE 1                                                         ______________________________________                                        EC COMPOSITIONS OF INVENTION                                                                  (1)  (2)    (3)    (4)  (5)                                   ______________________________________                                        (a) Diflufenican      2.6    2.6  2.6  2.8  2.6                                   Bromoxynil octanoate                                                                            37.1   37.1 37.1 --   37.1                                  MCPA Iso-octylester                                                                             --     --   --   42.0 --                                (b) Nonyl phenol ethoxylated                                                      phosphate ester                                                               (Rhodofac ® RE610)                                                                          5.0    5.0  5.0  --   5.0                                   (Rhodofac RM 710) --     --   --   6.0  --                                    Ethoxylated castor oil                                                        (Alkamuls ® EL 719)                                                                         5.0    5.0  5.0  6.0  5.0                               (c) N-Octyl pyrrolidone                                                           (Agsol ® EX 8)                                                                              22.6   22.6 25.2 25.9 25.2                                  N-Methyl pyrrolidone                                                          (Agsol ® EX 1)                                                                              --     5.1  --   4.3  --                                    Aromatic petroleum distillate                                                 (Aromatic 200) (Exxon)                                                                          5.1    --   --   --   20.1                                  Heptyl acetate                                                                (Exxate 700) (Exxon)                                                                            22.6   22.6 25.1 13.0 --                                    gamma-butyrolactone (BLO)                                                                       --     --   --   --   5.0                               ______________________________________                                    

                                      TABLE 2                                     __________________________________________________________________________    Stability of EC Compositions                                                  Upon Dilution with Water ((1:50)                                                             Appearance                                                              (1)   (2)   (3)   (4)  (5)                                           __________________________________________________________________________    Initial bloom                                                                          Excellent                                                                           Excellent                                                                           Excellent                                                                           Excellent                                                                          Excellent                                     After 20 inversions                                                                    Excellent                                                                           Excellent                                                                           Excellent                                                                           Excellent                                                                          Excellent                                     After 24 hrs                                                                           Excellent                                                                           Excellent                                                                           Excellent                                                                           Excellent                                                                          Excellent                                              (sl. trace                                                                          (sl. trace                                                                          (sl. trace (sl trace                                              ppt)  ppt)  ppt)       ppt)                                          After 4 days                                                                           Excellent                                                                           Excellent                                                                           Excellent                                                                           Excellent                                                                          Excellent                                              (Trace ppt)                                                                         (Trace ppt)                                                                         (Trace ppt)                                                                              (sl trace                                                                     ppt)                                          __________________________________________________________________________

What is claimed is:
 1. An emulsifiable concentrate (EC) which forms anaqueous micelle emulsion upon dilution with water in a 1:50 wt. ratio,which remains stable towards crystal formation during storage for atleast 4 days comprising, by weight:(a) about 20-60% of an admixture of alow dosage, water-insoluble fluorinated active agricultural chemical anda diluent active agricultural chemical, (b) about 2-15% of an anionicsurfactant and up to about 10% of a non-ionic surfactant, saidsurfactant system being sufficiently hydrophobic to keep the activeswithin the micelles instead of migrating into the water phase of theemulsion, (c) about 15-30% of a C₆ -C₁₈ alkyl pyrrolidone, and at leastone of the following: up to about 10% of a C₁ -C₄ alkyl pyrrolidone orgamma-butyrolactone, up to about 30% of a C₆ -C₈ alkyl acetate or anaromatic petroleum distillate.
 2. An EC according to claim 1 whereinsaid admixture comprises diflufenican as the fluorinated activeagricultural chemical and bromoxynil octanoate and/or isooctylmetachlorophenyl acetate as the diluent active agricultural chemical. 3.An EC according to claim 1 wherein said anionic surfactant is anethoxylated nonyl phenol phosphate ester.
 4. An EC according to claim 1wherein said non-ionic surfactant is an ethoxylated castor oil.
 5. An ECaccording to claim 1 wherein said C₆ -C₁₈ alkyl pyrrolidone is N-octylpyrrolidone.
 6. An EC according to claim 1 wherein said C₁ -C₄ alkylpyrrolidone is N-methyl pyrrolidone.